After complaining to Marge about serving dinner slowly, Homer goes to Moe's Tavern to watch the football match between Springfield Atoms and Boston Americans, where they meet Boston fans. The two fan groups start mocking each other, expecially after the mascot of the Boston team wins them the match by a touchdown, by cheating. After saying he's going to lose it if he sees a Boston fan after the way they won, back at home he's surprised by Bart wearing a Boston Americans hat.

Homer, trying to convince him to switch teams, take him around Springfield, but Bart refuses saying that the Boston people are his people. Startled, Homer starts hallucinating the Boston Americans team, and decides to take the family on a "hate-cation" to Boston, to show Bart how terrible the city is.

After the trip they arrive at Boston, where Homer starts provoking the people, but gets caught underneath a cart full of bobbleheads, and is saved by many doctors, learning of the healthcare in the city and being impressed by it. Afterwards, Marge, Lisa and Maggie explore the city on their own and learn about the beauty of the town, including an area for nerds that impress Lisa greatly.

Meanwhile, Homer and Bart go candlepin bowling, Homer being reclutant to try, but once he does he starts liking it more than bowling, and starts to see the good in Boston. Back at the hotel, happy with how the city turned out to be, the whole family decides to move to the town.

Homer finds a job at a candy factory that looks like the Power Plant and Lisa find herself liking the school and the teacher, however Bart finds out that detention in the school is not as much fun, as the kids in detention are seen singing instead of being the bad kids he expected. He finds out that the city is not made for him, but instead for intellectual and nerds like Lisa, so he tries to ruin the city for the family so they can move back home.

To do so, Bart takes the family on a parade for the last game won by cheating by the Boston Americans, where Homer tries not to get angry, but when offered a Boston Americans hat he couldn't resist and snaps it in half and start calling them cheaters. The family returns back to Springfield, with Marge being mad for making them leave, but Bart has now changed sides, while Lisa is hallucinating being still at Boston's school.

The episode was originally titled "Patriot Games", as seen in the script cover. However, the title was changed in January 2016 to "The Town".[1] A deleted scene showed Bart and Lisa outside a "Stawp & Shawp" (referencing Stop & Shop) with newspaper dispensers filled with The Herald newspapers.[2]